2-Decarboxy-2-tetrazolyl-13,14-dihydro-PG2 compounds

ABSTRACT

The present invention provides novel 2-decarboxy-2-tetrazolyl-13,14-dihydro-PG 2  compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a division of Ser. No. 026,066, filed Apr. 2,1979, now U.S. Pat. No. 4,243,611 issued Jan. 6, 1981.

BACKGROUND OF THE INVENTION

The present invention relates to novel prostaglandin analogs.Particularly, these compounds are analogs of the prostaglandins whereinthe C-20-C-19 position is unsaturated, i.e., 19,20-didehydro-PGcompounds. Most particularly, the present invention relates to novel2-decarboxy-2-tetrazolyl-13,14-dihydro-PG₂ compounds, a disclosure ofthe preparation and use of which is incorporated here by reference fromU.S. Ser. No. 025,899, filed Apr. 2, 1979, now 4,228,104, issued Oct.14, 1980.

PRIOR ART

Prostaglandin analogs exhibiting unsaturation in the C-17, C-18, or C-20position are known in the art. See, for example, U.S. Pat. No. 3,919,285German Offenlegungsschrift 2,635,985 (and its corresponding DerwentFarmdoc CPI No. 10302A), and U.S. Pat. No. 4,064,351 for examples ofsuch compounds. See also the reference cited in U.S. Ser. No. 026,066.

SUMMARY OF THE INVENTION

The present invention particularly provides: A compound of the formula##STR1## where D is (1) cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --,

(2) cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --,

(3) cis--CH₂ --CH═CH--CH₂ --C₂ --,

(4) trans-(CH₂)₃ --CH═CH--,

wherein Q is ##STR2## wherein R₅ is hydrogen or methyl, wherein R₂ ishydrogen, hydroxyl, or hydroxymethyl;

wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same ordifferent, with the proviso that one of R₃ and R₄ is fluoro only whenthe other is hydrogen or fluoro;

wherein W is ##STR3## and wherein X is --CH₂ CH₂ --.

The compounds of the present invention are particularly useful forinducing prostaglandin-like biological effects, as is described in U.S.Ser. No. 026,066. Uses of compounds in accordance with the presentinvention include, therefore, anti-asthmatic indication.

I claim:
 1. A compound of the formula ##STR4## wherein D is (1)cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --,(2) cis--CH═CH--CH₂ --(CH₂)_(g)--CF₂ --, (3) cis--CH₂ --CH═CH--CH₂ --CH₂ --, (4) trans--(CH₂)₃--CH═CH--,wherein g is zero, one, 2, or 3, wherein Q is ##STR5## whereinR₅ is hydrogen or methyl, wherein R₂ is hydrogen, hydroxyl, orhydroxymethyl; wherein R₃ and R₄ are hydrogen, methyl, or fluoro, beingthe same or different, with the proviso that one of R₃ and R₄ is fluoroonly when the other is hydrogen or fluoro; wherein W is ##STR6## andwherein X is --CH₂ CH₂ --.